Built detergent compositions containing dialkyl sulfoxides



United States Patent Ofilice 3,336,230 Patented Aug. 15, 1967 3,336,230BUILT DETERGENT COMPOSITIONS CON- TAlNlNG DIALKYL SULFOXIDES Warren I.Lyness, Mount Healthy, and David E. OConnor, Cincinnati, Ohio, assignorsto The Procter & Gamble Company, Cincinnati, Ohio, a corporation of OhioNo Drawing. Original application Mar. 10, 1965, Ser. No. 444,069, newPatent No. 3,288,858, dated Nov. 29, 1966. Divided and this applicationSept. 12, 1966, Ser. No. 578,510

4 Claims. (Cl. 252-138) ABSTRACT OF THE DISCLOSURE Detergentcompositions containing 0.5% to 90% dialkyl sulfoxide detergentscontaining ether linkages and 10% to 90% water soluble alkalinedetergency builders.

This application is a division of the copending application of Warren I.Lyness and David E. OConnor, Ser. No. 444,069, filed Mar. 30, 1965, nowUS. Patent 3,288,858.

This invention relates to sulfoxide compounds containing ether linkagesand to methods for synthesizing said compounds. Compounds containingboth a sulfoxide group and ether linkages are very useful surface activeagents.

' Normally sulfoxides are prepared by oxidizing the correspondingsulfide, however, this oxidation method is not desirable since theoxidation method normally produces a mixture of compounds containingsome unreacted sultides and/ or some sulfone by-products which aregenerally undesirable. It is diflicult or impossible to separate thesulfides and sulfones from the desired sulfoxides.

. It can be appreciated therefore than an effective method forintroducing a sulfoxide group and ether linkages into the same compoundis desirable. It can equally be appreciated that a method which permitsthe formation of compounds containing both ether linkages and sulfoxidegroups without the use of high temperatures, corrosive oxidizing agentsand specialized equipment is very desirable.

Accordingly, it is an object of this invention to prepare compoundscontaining both a sulfoxide group and ether linkage by methods whichavoid the aforesaid defects.

It is a more specific object of this invention to provide new sulfoxidescontaining ether linkages and having superior surface active properties.

It is a yet further object of this invention to provide detergentcompositions containing the sulfoxide detergents of this invention.

The objects of this invention can be accomplished by reacting a compoundhaving the formula wherein R is a hydrocarbon group containing from 1 toabout 30 carbon atoms, and wherein R is attached to the sulfur atom ofthe sulfoxide group by a single covalent bond between carbon and sulfur,wherein R and R are each selected from the group consisting of hydrogenand hydrocarbon groups containing from about 1 to about 30 carbon atoms,and wherein R, R and R each contain from to about linkages selected fromthe group consisting of ether, thioether and imino linkages, and from 0to about 5 amine groups each selected from the group consisting ofprimary, secondary and tertiary amine groups, and are not more reactivewith a strong base than a hydrogen atom attached to a saturated carbonatom adjacent to the sulfoxide group and wherein R and R are eachselected from the group consisting of hydrogen, aryl hydrocarbon groups,alkyl aryl hydrocarbon groups, alkyl hydrocarbon groups, and aliphaticring hydrocarbon groups, said R and R hydrocarbon groups each containingfrom 1 to about 30 carbon atoms and from 0 to about 10 linkages selectedfrom the group consisting of ether and thioether linkages, and wherein Qis an integer from 1 to about 50 and wherein Y is selected from thegroup consisting of 0 and 1, and wherein M is an alkali metal, with analkyl halide having the formula wherein X is selected from the groupconsisting of bromine, chlorine and iodine atoms and R is selected fromthe group consisting of hydrogen, alkyl, aryl and aryl substituted alkylhydrocarbon groups containing from 1 to about 30 carbon atoms.

This reaction proceeds as follows:

In R3 R4 9 RS ol: 3-:| [-(:1- :-o-] M R -OH2X R Y H H Q yields R1 R3 R4Nola haaalwns MX R2 YL. H H Q SULFOXIDE STARTING COMPOUNDS The sulfoxidestarting compounds in the above reaction and the formation of saidcompounds are described in detail in the copending application of WarrenI. Lyness and David E. OConnor, Ser. No. 448,228.

The symbol used for the sulfoxide groups is only a convenientrepresentation of the structure for purposes of the description of theinvention and is not necessarily indicative of the actual structurewhich is believed to involve a semi-polar bond. This symbol or evenmoresimple (SO-) is used hereinbefore and hereinafter to represent the'sulfoxide group.

As used herein, the term hydrocarbon groups refers to both unsubstitutedhydrocarbon groups and substituted hydrocarbon groups containing, forexample, ether linkages. Preferably the substituent hydrocarbon groups(R) in the formulas above and below are alkyl chains, straight orbranched, containing from 1 to about 22 carbon atoms (e.g., methyl,ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl,n-hexyl, n-heptyl, n-octyl, isooctyl, 2-ethylhexyl, diisobutyl, n-nonyl,tripropylene, n-decyl, undecyl, n-dodecyl, tridecyl, n-tetradecyl,pentadecyl, nhexadecyl, n-octadecyl, eicosyl, doc-osyl, vinyl, propenyl,octenyl, IO-undecenyl, 9-octadecenyl, cyclopentyl, cyclohexyl,cyclohexylmethyl, methylcyclohexyl, 2-cyclohexyldodecyl,12-cyclohexyldodecyl, 4-dodecylcyclohexyl and propynyl). Examples ofother groups include aryl groups containing 6 to 12 carbon atoms (e.g.,phenyl, diphenyl and naphthyl); and alkyl aryl groups containing benzeneor naphthalene groups with branched or straight alkyl chains of from 1to about 18 carbon atoms (e.g., benzyl, Lphenyl-dodecyl,l-methyl-Z-phenylethyl, Z-indenyl and naphthylmethyl). R R R and R areeach selected from the group consisting of hydrogen and hydrocarbongroups which are the same as those-examples given hereinbefore withrespect to R. The presence of certain non-reactive groups in or on thesubstituent, R, R R R or R groups is permissible. As an example ofnon-reactive groups, these substituent groups can contain up to about 10ether and/or thioether linkages. Up to five amino groups can be appendedto the chain or up to ten imino H (I I or N=) groups can form a part ofthe chain with open chain and/or cyclic configuration. (R, R and R havethe above definitions throughout the specification and claims.) Thus, R,R R R or R can represent, for example, such groups as3,6,9,l2,lS-pentathiaheptacosanyl; 3,6,9, 1111,15 pentaoxaheptacosanyl;3,6,9 trithiaheptacosauyl; 3,6,9 trioxaheptacosanyl; 2 dodecyloxyethyl;2 octadecyloxyethyl; 2-methoxyethyl; 2-ethoxyethyl; 2-hexyloxiyethyl;2-octyloxyethyl; 2-dodecylthioethyl; 2-octadecylthioethyl;Z-methylthioethyl; Z-ethylthioethyl; Z-hexylthioethyl; 2-octylthioethyl;ll-methoxyundecyl; ll-methylthloundecyl; ll-ethoxyundecyl; 9- or10-methoxyoctadecyl; 9- or l-ethoxyoctadecyl; 9- or I-methylthiooctadecyl; 2-, 3-, or 4-methoxycyclohexyl; 3 or4-methylthiocyclohexyl; 3-cyclohexyloxydecyl; 2,5, -p namethyl3,6,9,12,l pentaoxaheneicosanyl; 2 tetrahydrofuranyl;Z-tetrahydrothiophenyl; tetrahydropyranyl; 8 (tetrahydropyranyl) ethyl;[i (2 tetrahydro furanyl) (ethyl; tetrahydrothiofuranyl; 36 dioxaheptyl;3, 6 dithiaheptyl; 3,6,9 triazaheneicosanyl; l3 aminoethyl; Baminopropyl; t3 methylaminoethyl; ,8 methylamino propyl; [idimethylaminoethyl; 5 dimethylaminopropyl; 5 amino 3 azapentyl; 5dimethylamino 3 azapentyl; 5 dimethylamin-o 3 methazapentyl; 8 amino-3,6 diazaoctyl; 15 amino 3,6,9,12 tetrazapentadecyl; 4,6 dimethoxy 2 symtriazinyl; 4,6 diamino 2- sym triazinyl; 6 piperidyl; [3 (N piperidyl)ethyl; 13 (N piperazinyl) ethyl; [i (N imidazolyl) ethyl; ,8 (Nmorpholino) ethyl; ,8 (N oxazolyl) ethyl; ,B-(N-pyrrolidyD-ethyl; andZ-thiazolyl. Additionally, R can represent, for example,B-N-anilinoethyl; B-N-anilinopropyl; B- N pyridylethyl; 1 methoxy 2indanyl; fi-N-naphthyl-aminoethyl; 2-benzoxazolyl and4,6-dianilino-2-sym-triazinyl.

It will be understood that more than one sulfinyl carbanion group can bepresent in the molecule of component (A). This is to say there can bemore than one Preferably R and R in these additional groups are hydrogenatoms. The two sulfinyl carbanion groups should be separated by at leastthree aliphatic carbon atoms, but can be attached to adjacent carbonatoms on a benzene ring. Polymers containing multiple pendant alkalimetal sulfinyl carbanion groups are desirable as reactants. Therestriction on the number of carbon atoms which can be present in themolecule is, of course, dilferent when more alkali metal sulfinylcarbanion groups are present. The number of carbon atoms per alkalimetal sulfinyl carbanion group should not exceed 32, however.

The sodium and potassium salts of the above sulfoxide starting compoundsand mixtures thereof are preferred for stability and costconsiderations.

Y is zero in the above generic equation of the sulfoxide startingcompound when the sulfoxide starting compound is derived from alkalimetal alkanesulfenates and Y is 1 when the sulfoxide starting compoundis derived from alkali metal salts of sulfinyl carbanions. Q varies inthe above formula depending on the number of moles of the epoxycompounds, of the same or different structures, that are reacted withthe aforementioned salts of sulfinyl carbanions and alkanesulfenates toprepare the sulfoxide starting compounds of this invention. Mixtures ofcompounds wherein Y is 0 and 1, and/or where Q varies within the range 1to 50, can be used.

Preferred sulfoxide starting compounds are those in which R is a methylgroup, R R and R are hydrogen atoms, Y and Q are both 1, and R is analkyl chain containing from about 8 to about 20 carbon atoms. Otherpreferred sulfoxide starting compounds are those in which R is also ahydrogen atom. In preferred methods, those sulfoxide starting compoundscontaining a long alkyl chain group or other hydrophobic group or groupsare reacted with short chain alkyl halides and those sulfoxide compoundscontaining no long hydrophobic group are reacted with alkyl halidescontaining a long hydrophobic group.

THE ALKYL HALIDE COMPOUNDS The alkyl portions of R can contain from 0 toabout 10 linkages selected from the group consisting of ether andthioether linkages. Any branched, ring, or straight chain hydrocarbon,whether saturated or unsaturated, containing a halogen atom attached toa primary, saturated alkyl carbon atom and fitting the descriptionhereinbefore given will react in the above manner. Permissiblesubstituent groups on these hydrocarbons include ether and thioetherlinkages. Examples of alkyl halide reactants suitable for use with thesalts of sulfinyl carbanions include dodecyl bromide, dodecyl chloride,ncopentyl chloride, docosyl bromide, octadecyl bromide, hexadecylbromide, hexadecyl chloride, hexyl bromide, 3-(chloromethyl) heptane,amyl chloride, iso-amyl chloride, methyl chloride, methyl iodide, ethylbromide, tetradecyl bromide, alkyl chloride,1-bromo-3,6,9-trioxaheneicosane, 1-bromo-3,6,9,l2-tetraoxatetracosane,benzyl chloride, 2- phenylethyl bromide, cyclohexylmethyl chloride, 3-pentenyl bromide, 9-octadecenyl bromide, l0-undecenyl bromide,l-chloro-2-methoxydodecane, 9- or IO-methoxyoctadecyl bromide, 9- orlO-methylthiooctadecyl bromide, and 1-chloro-3,6-dioxaheptane. Theproducts of these reactions either have useful and desirable surfaceactive (including detergent) properties or are useful as intermediatesin the preparation of surface active compounds.

It will be understood that the alkyl halide compounds of this inventioncan contain more than one CH X group so long as the carbon of R joins Rto the rest of the R group by single covalent bonds and so long as thehalogen atoms are not attached to the same carbon atom or to adjacentcarbon atoms. The presence of additional reactive sites simply allowsthe alkyl halide compound to react with more than one mole of sulfoxidestarting compounds as hereinbefore described.

Preferred alkyl halide compounds are those containing an alkyl chaincontaining from about 8 to about 20 carbon atoms. When the sulfoxidestarting compound has a long alkyl chain or other hydrophobic group orgroups, methyl, ethyl and propyl halides are preferred reactants.

CONDITIONS OF THE REACTION Dimethyl sulfoxide is an excellent solventfor the reactions of this invention and in most instances an excess ofdimethyl sulfoxide is the preferred solvent. However, other non-reactivesolvents or diluents can be used, especially other sulfoxide compounds.These solvents preferably should not contain any, reactive constituenteither as part of the structure of the solvent or as part of impuritiespresent in the solvent if maximum yields are desired. The use ofsolvents which will react with the primary reactants of this inventionis generally undesirable. Suitable non-reactive solvents or diluents forthe above reactions of sulfoxide starting compounds and alkyl halidecompounds are to be found in such classes of compounds as the aliphaticor aromatic hydrocarbons, aliphatic, aromatic or mixedaliphatic-aromatic ethers, cyclic ethers and amines. Examples ofsuitable non-reactive hydrocarbon solvents include hexane, petroleumether, Stoddard solvent, benzene, toluene and mixed xylenes. Among theether compounds which are suitable as solvents are diethyl ether,dibutyl ether, anisole, diphenyl ether, tetrahydrofuran,1,2-dimethoxyethane and diethylene glycol dimethyl ether. Aminecompounds which can serve as solvents for the reactions of thisinvention include butylamine, N-methyl butylamine, anhydrous ethylenediamine, pyridine and morpholine. Anhydrous liquid ammonia can also beused as a solvent. Still another compound which is suitable isN,N-dimethyl formamide. Other similar non-reactive solvents or diluentscan be used with substantially equivalent results.

The rate and course of the above reactions can be affected by the choiceof solvent. The use of mixtures of two or more non-reactive compounds asthe reaction medium is, of course, suitable and in some cases preferableto the use of a single species. A temperature range of about C. to about100 C. is suitable for carrying out reactions of this invention.

THE SULFOXIDE COMPOUNDS OF THIS INVENTION The products of this reactionare unique in that they are generally obtained in a much purer statethan might be possible by any known synthesis techniques which might beapplied. As a consequence, they are less likely to have an odor or tocontain ineffective or undesirable by-products.

The sulfoxide compounds of this invention which contain ether linkageshave the general formula R R R R Y O E Q wherein R is a hydrocarbongroup containing from 1 to about 30 carbon atoms, and wherein R isattached to the sulfur atom of the sulfoxide group by a single covalentbond between carbon and sulfur, wherein R and R are each selected fromthe group consisting of hydrogen and hydrocarbon groups containing fromabout 1 to about 30 carbon atoms, and wherein R, R and R each containfrom 0 to about 10 linkages selected from the group consisting ofether,thioether and imino linkages, and from 0 to about amine groupseach selected from the group consisting of primary, secondary 'andtertiary amine groups, and are not more reactive with a strong base thana hydrogen atom attached to a saturated carbon atom adjacent to thesulfoxide group and wherein R and R are each selected from the groupconsisting of hydrogen, aryl hydrocarbon groups, alkyl aryl hydrocarbongroups, alkyl hydrocarbon groups, and aliphatic ring hydrocarbon groups,said R and R hydrocarbon groups containing from 1 to about 30 carbonatoms and from 0 to about linkages selected from the group consisting ofether and thioether linkages, and wherein Q is an integer from 1 toabout 50 and wherein Y is selected from the group consisting of 0 and 1,and wherein R is selected from the group consisting of hydrogen, alkyl,aryl, and aryl substituted alkyl hydrocarbon groups containing from 1 toabout 30 carbon atoms.

DETERGENT COMPOSITIONS The novel sulfoxide of this invention whichcontain ether linkages are useful per se as detergent and surface activecompounds or as intermediates in the preparation of detergent andsurface active compounds. They are very mild to the skin.

The uses to which surface active compounds can be put are numerous andwell known, e.g., preparing oil-1nwater emulsions, textile treatment,dyeing, flotation, preparation of rubber latex, and the like.

The detergent compositions of this invention contain from about 0.5% toabout 90% of a preferred sulfoxide material having the formula 6 whereinat least one of the group R, R R R R and R is an alkyl group containingfrom about 8 to about 18 carbon atoms and from 0 to about 10 otherlinkages, the

remaining groups being selected from the group consisting of hydrogenand alkyl groups containing from 1 to about 3 carbon atoms, the totalnumber of carbon atoms in the molecule being from about 12 to about 32carbon atoms.

Desirably, but not necessarily, the sulfoxide compounds of thisinvention are used with alkaline builder materials to form builtdetergent compositions, as for example, liquid, bar, flake, granular ortabletted granular compositions. Such compositions have enchanceddetergent characteristics due to coaction in aqueous washingcompositions between the hydroxy sulfoxides and the alkaline buildermaterial.

The compositions of this invention contain from 0% to 90%, preferablyfrom about 10% to about 90%, of water soluble alkaline detergencybuilder salts, either of the organic or inorganic types, and shouldprovide a washing solution pH of about 9 to about 12. The ratio ofbuilder salts to organic detergent is preferably from about 1:4 to about20:1. Examples of water soluble inorganic alkaline detergency buildersalts are alkali metal carbonates, phosphates, polyphosphates andsilicates. Specific examples of such salts are sodium and potassiumtripolyphosphates, carbonates, pyrophosphates, orthophosphates andhexarnetaphosphates. Examples of organic alkaline detergency buildersalts are (1) alkali metal amino polycarboxylates [e.g., sodium andpotassium ethylenediaminetetraacetates,N-(Z-hydroxyethyl)-ethylenediaminetriacetates, nitrilo triacetates, andN-(2-hydroxyethyl)-nitrilo diacetates]; (2) alkali metal salts of phyticacid (e.g., sodium and potassium phytatessee US. Patent 2,739,- 942);(3) water soluble salts of ethane-1-hydroxy-1,1-diphosphonate (e.g., thetrisodium and tripotassiuml sa1ts see US. Patent 3,159,581); (4) watersoluble salts of methylene diphosphonic acid (e.g., trisodium andtripotassium methylene diphosphonate and the other salts described inthe copending application of Francis L. Diehl,

Ser. No. 266,025, filed Mar. 18, 1963); (5) water soluble salts ofsubstituted methylene diphosphonic acids (e.g.,

trisodium and tripotassium ethylidene, isopropylidene,

benzylmethylidene, and halomethylidene diphosphonates and the othersubstituted methylene diphosphonates disclosed in the copendingapplication of Clarence H. Roy, Ser. No. 266,055, filed Mar. 18, 1963);(6) water soluble salts of polycarboxylate polymers and copolymers asdescribed in the copending application of Francis L. Diehl, Ser. No.269,359, filed Apr. 1, 1963 (e.g., polymers of itaconic acid, aconiticacid; maleic acid; mesacon-ic acid; fumaric acid; methylene malonicacid; and citronic acid and copolymers with themselves and othercompatible monomers such as ethylene); and (7) mixtures thereof.

Mixtures of organic and/or inorganic builders can be used and aregenerally desirable. Especially preferred are the mixtures of buildersdisclosed in the copending application of Burton H. Gedge, Ser. No.398,705, filed Sept. 23, 1964 (e.g., ternary mixtures of sodiumtripolyphosphate, sodium nitrilotriacetate, and trisodiumethanel-hydroxy-1,1-diphosphonate) The detergent compositions of thisinvention can contain any of the usual adjuvants, diluents andadditives, for example, anionic, nonionic, ampholytic, cationic orzwitterionic detergents, perfumes, anti-tarnishing agents,anti-redeposition agents, bacteriostatic agents, dyes, fluorescers, sudsbuilders, suds depressors, and the like, without detracting from theadvantageous properties of the composition. Examples of anionicdetergents are sodium coconut soap, sodium dodecylbenzene sulfonate andpotassium tallow alkyl sulfate. Examples of nonionicdetergents aredodecyldimethylamine oxide and the condensation product of coconut fattyalcohol with 5.5 moles of ethylene oxide. An example of a zwitterionicdetergent is 3-(N,N-

dimethyl-N-hexadecylammonio -2-hydroxypropane- 1-sulfonate. An exampleof an ampholytic detergent is sodium 3-dodecylaminopropionate. Anexample of a cationic detergent is cetyltrimethylammonium bromide.

It is believed that the sulfoxide surface active agents of thisinvention are suds builders for conventional anionic detergents.

Normally the organic detergent components, the builders and the minoringredients are incorporated into the composition prior to conversioninto final product form, e.g., detergent granules, flakes, etc., butthey can also be added individually in the form of particles or asliquids.

All percentages, ratios and parts herein are by weight unless otherwisespecified.

The practice of the present invention is set forth in the followingexamples.

Example 1 Dodecene-l-oxide (0.1 mole) was added dropwise over a two-hourperiod to a solution of sodium methylsulfinylcarbanion (0.1 mole) indimethyl sulfoxide at room temperature and the mixture was stirred fortwo hours, at which time the reaction was essentially complete. Afterthe reaction mixture was allowed to stand overnight at room temperature,the product which had the formula CioHzrCH-CHz-CHzS CH was reacted withmethyl iodide (0.1 mole) which was added dropwise to the reactionmixture. The mixture was stirred for two hours at which time thereaction was essentially complete. The mixture was allowed to standovernight at room temperature and the water was added. The mixture wasextracted with methyl acetate, the extracts were dried and the solventwas stripped off. The residue was distilled to obtain a 66% yield of3-methoxytridecyl methyl sulfoxide (BR 175 /0.7 mm.).

The 3-methoxytridecyl methyl sulfoxide is useful as a detergentsurfactant.

When in the above example the following groups are substituted for themethyl group and/or the hydrogen atoms in the CH group adjacent to thesulfinyl group and/or one of the hydrogen atoms in the CH group adjacentto the alkoxide group and/or the dodecyl group in the above alkoxidecompound so that the total number of carbon atoms in the resultingalkali metal alkoxide compound is less than 32 and so that there are nomore than two aromatic groups present in the molecule, substantially thesame results are achieved in that the corresponding alkali metalalkoxides react with the alkyl halide compounds to produce thecorresponding alkoxy alkyl alkyl sulfoxides: methyl; ethyl; n-propyl;isopropyl; n-butyl; isobutyl; n-pentyl; isopentyl; n-hexyl; n-heptyl;n-octyl; isooctyl; 2-ethylhexyl; diisobutyl; n-nonyl; tripropylene;n-decyl; undecyl; n-dodecyl; tridecyl; n-tetradecyl; pentadecyl;n-hexadecyl; n-octadecyl; eicosyl; docosyl; vinyl; propenyl; octenyl;IO-undecenyl; 9-octadecenyl; cyclopentyl; cyclohexyl; cyclohexylmethyl;methylcyclohexyl; Z-cyclohexyldodecyl; 12-cyclohexyldodecyl;4-dodecylcyclohexyl; propynyl; phenyl; biphenyl; naphthyl; benzyl; 2-phenyl-dodecyl; l-methyl-Z-phenylethyl; Z-indenyl; naphthylmethyl;3,6,9,12,15-pentathiaheptacosanyl; 3,6,9,l2,IS-pentaoxaheptacosanyl;3,6,9-11rithiaheptacosanyl; 3,6,9 trioxaheptacosanyl; 2-dodecyloxyethyl;2-octadecyloxyethyl; 2-methoxyethyl; 2-ethoxyethyl; 2-hexyloxyethyl;2-octyloxyethyl; 2-dodecylthioethyl; 2- octadecylthioethyl;2-methylthioethyl; 2-ethylthioethyl; 2-hexylthioethyl; 2-octylthioethyl;ll-methoxyundecyl; 11 methylthioundecyl; 11 ethoxyundecyl; 9- or 10-methoxyoctadecyl; 9- or lO-ethoxyoctadecyl; 9- or 10-methylthiooctadecyl; 2-, 3-, or 4-methoxycyclohexyl; 3- or4-methylthiocyclohexyl; 3-cyclohexyloxydecyl; 2,5,8, 11,14-pentamethyl-3,6,9,12,15 pentaoxaheneicosanyl;

Z-tetrahydrofuranyl; 2-tetrahydrothiophenyl; tetrahydropyranyl;fi-(tetrahydropyranyl)-ethyl; 5 (Z-tetrahydrofuranyl-ethyl;tetrahydrothiouranyl; 3,6-dioxaheptyl; 3,6- dithioheptyl; 3,6,9triazeheneicosanyl; B aminoethyl; B aminopropyl; ,8 methylaminoethyl; Bmethylarninopropyl; fi-dimethylaminoethyl; ,8 dimethylaminopropyl; 5amino 3 azapentyl; 5 dimethylamino-3-azapentyl;5-dimethylamino-3-methazapentyl; 8 amino 3,6 diazaoctyl;l5-amino-3,6,9,12 tetrazapentadecyl; 4,6 dimethoxy 2 sym triazinyl;4,6-diamino-2-sym-triazinyl; 4-piperidyl; fi-(N-piperidyD-ethyl; {3(N-piperazinyl) ethyl; fl-(N-imidazolyD-ethyl; fi-(N-morpholino)-ethyl;,8 (N-oxazolyl) ethyl; B-(N-pyrrolidyl)- ethyl; 2-thiazolyl;3-(N-anilino)-ethyl; ,B-N-anilinopropyl; fi-N-pyridylethyl; 1 methoxyZ-indanyl; B-N-naphthylaminoethyl; 2 benzoxazolyl; 4,6dianilino-2-sym-triazinyl; and mixtures thereof.

When in the above example the corresponding potassium and lithium saltsof the alkoxide are substituted either wholly or in part for the sodiumsalts, substantially the same results are achieved in that the reactionwith the alkyl halide compound follows essentially the same path.

When in the above examples the following alkyl halides are substitutedeither wholly or in part for the methyl halide in the above reaction,substantially the same results are obtained in that the alkoxide ion isalkylated with the alkyl group from the following alkyl halidereactants: neopentyl chloride, docosyl bromide, hexadecyl bromide,hexadecyl chloride, 3-(chloromethyl) heptane, amyl chloride, iso-amylchloride, methyl chloride, dodecyl bromide, ethyl bromide, tetradecylbromide, alkyl chloride, l-bromo- 3,6,9 trioxaheneicosane, 1bromo-3,6,9,12-trioxatetracosane, benzyl chloride, 2-phenylethylbromide, cyclohexylmethyl chloride, 3-pentenyl bromide, 9-octadecenylbromide, IO-undecenyl bromide, 9- or IO-methoxyoctadecyl bromide, 9- orIO-methylthiooctadecyl bromide, l-chloro- 3,6-dioxaheptane, and mixturesthereof.

When in the above examples the following solvents are substituted eitherwholly or in part for the dimethyl sulfoxide, substantially equivalentresults are obtained in that the same reactions occur: benzene,1,2-dimethoxy ethane, hexane, petroleum ether, xylenes, diphenyl ether,tetrahydrofuran, butylamine, N,N-dimethyl formamide, or diethyleneglycol dimethyl ether (digylme), Stoddard solvent, toluene, pyridine,diethyl ether, dibutyl ether, anisole, N-methyl butylamine, anhydrousethylene diamine, morpholine, anhydrous liquid ammonia, and mixturesthereof.

When the 3-methoxytridecyl methyl sulfoxide and the other surface activesulfoxides of the above examples are used with the following detergencybuilders with a ratio of a builder to a detergent surfactant of about 2/2 :1 and at a detergent surfactant concentration in water of about0.02% by weight, excellent detergency effects are obtained.

When in the above examples tripolyphosphates; pyrophosphates; ethylenediarninetetraacetates; N-(Z-hydroxyethyl)-ethylenediamine triacetates;nitrilo triacetates; N- (2-hydroxyethyl)-nitrilodiacetates; phytates;ethane-l-hydroxy-l-diphosphonates; methylenediphosphonates; ethylidenediphosphonates; isopropylidene diphosphonates; benzylmethylidenediphosphonates; chloromethylidene diphosphonates; salts of polymers ofitaconic acid, aconitic acid, maleic acid, mesaconic acid; fumaric acid,methylene maleic acid and citraconic acid; salts of copolymers of theabove acids with themselves; salts of copolymers of the above acids withethylene; salts of copolymers of the above acids with themselves andethylene (the foregoing named polymers and copolymers have molecularweights of at least 350 and equivalent weights of from 50 to based onthe acid forms); and mixtures thereof in the form of their sodiumpotassium, triethanolammonium, diethanolammonium andmonoethanolam-monium salts and mixtures thereof.

What is claimed is:

1. Detergent compositions consisting essentially of from about 0.5% toabout 90% of a material having the formula R2 H H wherein at least oneof the group R, R R R R and R is an alkyl or alkoxyalkyl groupcontaining from about 8 to about 18 carbon atoms and wherein thealkoxyalkyl group contains from 1 to about 10 ether linkages, theremaining groups being selected from the group consisting of hydrogenand alkyl groups containing from 1 to about 3 carbon atoms, the totalnumber of carbon atoms in the molecule being from about 12 to about 32carbon atoms, and from about 10% to about 90% of water soluble alkalinedetergency builder salts.

2. The detergent composition of claim 1 wherein the said material is3-methoxytridecyl methyl sulfoxide.

3. The detergent composition of claim 1 wherein the References CitedUNITED STATES PATENTS 2,787,595 4/1957 Webb 252138 2,846,401 8/1958McCarthy et al 252-138 3,124,618 3/1964 Berry 260607 3,146,271 8/1964Louthan 26O607 OTHER REFERENCES Wagner and Zook: Synthetic OrganicChemistry," Chapman and Hall, p. 226 (1953).

LEON D. ROSDOL, Primary Examiner.

S. E. DARDEN, Examiner.

1. DETERGENT COMPOSITIONS CONSISTING ESSENTIALLY OF FROM ABOUT 0.5% TOABOUT 90% OF A MATERIAL HAVING THE FORMULA